Tert-butyl 4-((6-(5-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)pyrazin-2-yl-amino)pyrimidin-4-ylamino)methyl)piperidine-1-carboxylate → HCID 42610781, compound

HRID 384645Notes

Reaction equation

HRID 384645 reaction equation
[Si]([O:8][CH2:9][C:10]#[C:11][C:12]1[N:13]=[CH:14][C:15]([NH:18][C:19]2[N:24]=[CH:23][N:22]=[C:21]([NH:25][CH2:26][CH:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]3)[CH:20]=2)=[N:16][CH:17]=1)(C(C)(C)C)(C)C>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[NH:30]1[CH2:31][CH2:32][CH:27]([CH2:26][NH:25][C:21]2[N:22]=[CH:23][N:24]=[C:19]([NH:18][C:15]3[N:16]=[CH:17][C:12]([C:11]#[C:10][CH2:9][OH:8])=[N:13][CH:14]=3)[CH:20]=2)[CH2:28][CH2:29]1

Participants

3

Reactant 1

HCID 66746379Tert-butyl 4-((6-(5-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)pyrazin-2-yl-amino)pyrimidin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 42610781HCID 42610781, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

Crude tert-butyl 4-((6-(5-(3-(tert-butyldimethylsilyloxy)prop-1-ynyl)pyrazin-2-ylamino)pyrimidin-4-ylamino)-methyl)piperidine-1-carboxylate (0.15 mmol) was dissolved in tetra n-butylammonium fluoride (1M in THF, 225 μL). After 30 minutes the solution was evaporated and the residue was purified by preparative HPLC. The resulting solid was dissolved in 30% trifluoroacetic acid in dichloromethane and stirred at room temperature for 30 minutes. The mixture was adsorbed onto then MP-TsOH SPE cartridge and eluted with 2M ammonia in methanol. The basic fractions were concentrated to give 3-(5-(6-(piperidin-4-ylmethylamino)pyrimidin-4-ylamino)pyrazin-2-yl)prop-2-yn-1-ol (7.8 mg, 7.5% over two steps) as a white solid.

Workup

  1. customAfter 30 minutes the solution was evaporated
  2. customthe residue was purified by preparative HPLC
  3. dissolutionThe resulting solid was dissolved in 30% trifluoroacetic acid in dichloromethane
  4. washeluted with 2M ammonia in methanol
  5. concentrationThe basic fractions were concentrated

Sources & evidence

ORD record
ord-2c4d0d2288d5477eb1ee5c8ef89b12b0
Source dataset
uspto-grants-2013_02
Patent number
US08367658B2

Reaction notes

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